U.S. Pat. No. 4,209,621, issued Jun. 24, 1980, discloses substituted phenyl-1,2,4-triazolo[1,5-a]pyrimidines of the formula ##STR1## wherein R.sub.1 is H or alkyl as anxiolytic agents.
French Patent 1,433,798, published Feb. 21, 1966, (U.S. priority May 1, 1964), discloses 7-hydroxy-5-methyl-1,2,4-triazolo[1,5-a]pyrimidine as a herbicide.
EP-A-220,458, published May 6, 1987 (German priority Sep. 28, 1985) and EP-A-217,218, published Apr. 8, 1987 (German priority. Sep. 28, 1985), disclose herbicidal triazolopyrimidines of the formula ##STR2##
EP-A-215,382, published Mar. 25, 1987 (German priority Sep. 17, 1985), discloses herbicidal 7-aminoazolo[1,5-a]pyrimidines of the formula ##STR3## wherein A is N, CH, C(alkyl) CBr or CCl.
U.S. Pat. No. 4,740,233, issued Apr. 26, 1988, discloses herbicidal triazolopyrimidines of the formula ##STR4## wherein R.sub.1 includes phenyl and substituted phenyl.
J. Fac. Agric. Kyushu Univ. 1977, 21 (2-3), 99-105 discloses herbicidal triazolopyrimidines of the formula ##STR5## wherein R.sub.1 is H, SCN, SCH.sub.3, Ph or CH.sub.3 ;
R.sub.2 is H or CH.sub. 3; and PA1 R.sub.3 is SH, SCH.sub.2 Ph or SCH.sub.2 CO.sub.2 H. PA1 R.sub.1 is C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.2 -C.sub.4 alkoxyalkyl, C.sub.2 -C.sub.4 alkenyl, C.sub.2 -C.sub.4 alkynyl, PA1 C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 alkylthio, halogen, CN, PA1 C.sub.2 -C.sub.4 alkylcarbonyl, C.sub.1 -C.sub.4 alkylamino, PA1 C.sub.2 -C.sub.4 dialkylamino or C.sub.2 -C.sub.4 alkylthioalkyl; PA1 R.sub.2 is halogen, NO.sub.2, OR.sub.3, S(O).sub.n R.sub.3, OSO.sub.2 R.sub.3, C.sub.1 -C.sub.4 haloalkyl, C.sub.3 -C.sub.4 halocycloalkyl, C.sub.3 -C.sub.4 haloalkynyl or C.sub.2 -C.sub.4 haloalkenyl; PA1 R.sub.3 is C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.2 -C.sub.4 alkenyl, C.sub.2 -C.sub.4 haloalkenyl, C.sub.3 -C.sub.4 alkynyl, C.sub.3 -C.sub.4 haloalkynyl, or C.sub.3 -C.sub.4 halocycloalkyl: PA1 R.sub.4 is H, halogen, C.sub.1 -C.sub.3 alkoxy, C.sub.1 -C.sub.3 alkyl or CF.sub.3 ; PA1 R.sub.5 is H, halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.2 -C.sub.4 alkoxyalkyl, C.sub.2 -C.sub.4 alkenyl, C.sub.2 -C.sub.4 alkynyl, NO.sub.2, OR.sub.3, S(O)nR.sub.3, OSO.sub.2 R.sub.3, phenyl, phenoxy, C.sub.2 -C.sub.4 alkoxycarbonyl, C.sub.2 -C.sub.4 alkylcarbonyl, CN, NHSO.sub.2 CF.sub.3, C.sub.2 -C.sub.4 haloalkenyl, C.sub.3 -C.sub.4 haloalkynyl, C.sub.2 -C.sub.4 dialkylamino, or C.sub.3 -C.sub.4 halocycloalkyl; PA1 n is 0, 1 or 2; PA1 R.sub.6 is H or F; PA1 X, Y and Z are independently CR.sub.7 or N; and PA1 R.sub.7 is H, CN, halogen, NO.sub.2, CO.sub.2 R.sub.3, C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.3 haloalkyl or CONH.sub.2 ; PA1 G is CH and G.sup.1 is N (Formula Ia); or PA1 G is N and G.sup.1 is CH (Formula Ib). ##STR7## 2. Compounds of Preferred 1 wherein Formula I is Ia; PA1 X is CR.sub.7 ; PA1 Y is N; and PA1 Z is N. PA1 Formula I is Ib; PA1 X is CR.sub.7 ; PA1 Y is N; and PA1 Z is N. PA1 Formula I is Ia; PA1 X is N; PA1 Y is CR.sub.7 ; and PA1 Z is N. PA1 Formula I is Ib; PA1 X is N; PA1 Y is CR.sub.7 ; and PA1 Z is N. PA1 Formula I is Ia; PA1 X is N; PA1 Y is N; and PA1 Z is CR.sub.7. PA1 Formula I is Ib; PA1 X is N; PA1 Y is N; and PA1 Z is CR.sub.7. PA1 Formula I is Ia; PA1 X is N; PA1 Y is N; and PA1 Z is N. PA1 Formula I is Ib; PA1 X is N; PA1 Y is N; and PA1 Z is N. PA1 R.sub.6 is H; and PA1 R.sub.1 is C.sub.1 -C.sub.3 alkyl, SCH.sub.3, NHCH.sub.3, CHO.sub.2 CH.sub.3 or CH.sub.2 SCH.sub.3. PA1 R.sub.2 is CF.sub.3, SCF.sub.3, SCF.sub.2 H, OCF.sub.3, OCH.sub.2 CHF.sub.2, OCH.sub.2 CF.sub.3, OCF.sub.2 H, CF.sub.2 CF.sub.3, CF.sub.2 Cl, CHF.sub.2, CH.dbd.CF.sub.2 or 2,2-difluorocyclopropane. PA1 R.sub.3 is CH.sub.2 CH.sub.2 F, CH.sub.2 CF.sub.3, CH(CH.sub.3)CF.sub.3, CH.sub.2 CH.sub.2 CF.sub.3, CH.sub.2 CHF.sub.2, CF.sub.3 or CF.sub.2 H; and PA1 R.sub.4 is H. PA1 R.sub.5 is H, halogen, OCH.sub.3, OCF.sub.2 H, OCH.sub.2 CF.sub.3, SCF.sub.3, C.sub.1 -C.sub.3 alkyl, OCF.sub.3, OCH.sub.2 CHF.sub.2, OCH.sub.2 CF.sub.3, OCH.sub.2 CH.sub.2 F, SCHF.sub.2, CF.sub.3, CHF.sub.2, CF.sub.2 Cl, CH.sub.2 CF.sub.3, CH.sub.2 F, CCl.sub.3, CH.sub.2 Cl or CN and R.sub.5 is in the meta position. PA1 R.sub.1 is C.sub.1 -C.sub.3 alkyl. PA1 R.sub.1 is C.sub.1 -C.sub.3 alkyl; PA1 R.sub.2 is CF.sub.3, SCF.sub.3, SCF.sub.2 H, OCF.sub.3, OCH.sub.2 CHF.sub.2, OCH.sub.2 CF.sub.3, OCF.sub.2 H, CF.sub.2 CF.sub.3, CH.sub.2 Cl, CHF.sub.2, CH.dbd.CF.sub.2 or 2,2-diflurocyclopropane; PA1 R.sub.3 is CH.sub.2 CH.sub.2 F, CH.sub.2 CF.sub.3, CH(CH.sub.3)CF.sub.3, CH.sub.2 CH.sub.2 CF.sub.3, CH.sub.2 CHF.sub.2, CF.sub.3 or CF.sub.2 H; PA1 R.sub.4 is H; PA1 R.sub.5 is H, halogen, OCH.sub.3, OCF.sub.2 H, OCH.sub.2 CF.sub.3, SCF.sub.3, C.sub.1 -C.sub.3 alkyl, OCF.sub.3, OCH.sub.2 CHF.sub.2, OCH.sub.2 CH.sub.2 F, SCHF.sub.2, CF.sub.3, CHF.sub.2, CF.sub.2 Cl, CH.sub.2 CF.sub.3, CH.sub.2 F, CCl.sub.3, CH.sub.2 Cl or CN and R.sub.5 is in the meta position; and PA1 R.sub.6 is H. PA1 R.sub.1 is C.sub.1 -C.sub.3 alkyl; PA1 R.sub.2 is CF.sub.3, SCF.sub.3, SCF.sub.2 H, OCF.sub.3, OCH.sub.2 CHF.sub.2, OCH.sub.2 CF.sub.3, OCF.sub.2 H, CF.sub.2 CF.sub.3, CH.sub.2 Cl, CHF.sub.2, CH.dbd.CF.sub.2 or 2.2-diflurocyclopropane; PA1 R.sub.3 is CH.sub.2 CH.sub.2 F, CH.sub.2 CF.sub.3, CH(CH.sub.3)CF.sub.3, CH.sub.2 CH.sub.2 CF.sub.3, CH.sub.2 CHF.sub.2, CF.sub.3 or CF.sub.2 H; PA1 R.sub.4 is H; PA1 R.sub.5 is H, halogen, OCH.sub.3, OCF.sub.2 H, OCH.sub.2 CF.sub.3, SCF.sub.3, C.sub.1 -C.sub.3 alkyl, OCF.sub.3, OCH.sub.2 CHF.sub.2, OCH.sub.2 CH.sub.2 F, SCHF.sub.2, CF.sub.3, CHF.sub.2, CF.sub.2 Cl, CH.sub.2 CF.sub.3, CH.sub.2 F, CCl.sub.3, CH.sub.2 Cl or CN and R.sub.5 is in the meta position; PA1 R.sub.6 is H; and PA1 R.sub.7 is CN. PA1 R.sub.1 is C.sub.1 -C.sub.3 alkyl; PA1 R.sub.2 is CF.sub.3, SCF.sub.3, SCF.sub.2 H, OCF.sub.3, OCH.sub.2 CHF.sub.2, OCH.sub.2 CF.sub.3, OCF.sub.2 H, CF.sub.2 CF.sub.3, CH.sub.2 Cl, CHF.sub.2, CH.dbd.CF.sub.2 or 2,2-diflurocyclopropane; PA1 R.sub.3 is CH.sub.2 CH.sub.2 F, CH.sub.2 CF.sub.3, CH(CH.sub.3)CF.sub.3, CH.sub.2 CH.sub.2 CF.sub.3, CH.sub.2 CHF.sub.2, CF.sub.3 or CF.sub.2 H; PA1 R.sub.4 is H; PA1 R.sub.5 is H, halogen, OCH.sub.3, OCF.sub.2 H, OCH.sub.2 CF.sub.3, SCF.sub.3, C.sub.1 -C.sub.3 alkyl, OCF.sub.3, OCH.sub.2 CHF.sub.2, OCH.sub.2 CH.sub.2 F, SCHF.sub.2, CF.sub.3, CHF.sub.2, CF.sub.2 Cl, CH.sub.2 CF.sub.3, CH.sub.2 F, CCl.sub.3, CH.sub.2 Cl or CN and R.sub.5 is in the meta position; PA1 R.sub.6 is H; and PA1 R.sub.7 is CN.
J. Fac. Agric. Kyushu Univ. 1975, 19(2-3), 91-102 discloses s-triazolo[1,5-a]pyrimidines with herbicidal activity.
The present invention is patentably distinguishable over the foregoing at least in the substitution on the azole and/or the pyrimidine functionality.